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[ CAS No. 267875-62-7 ] {[proInfo.proName]}

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Chemical Structure| 267875-62-7
Chemical Structure| 267875-62-7
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Product Details of [ 267875-62-7 ]

CAS No. :267875-62-7 MDL No. :MFCD06656839
Formula : C14H18N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KXLKVGMKXJWVMZ-UHFFFAOYSA-N
M.W : 246.30 Pubchem ID :29946181
Synonyms :

Safety of [ 267875-62-7 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 267875-62-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 267875-62-7 ]

[ 267875-62-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 1314538-55-0 ]
  • [ 17422-32-1 ]
  • [ 267875-62-7 ]
  • 2
  • tert-butyl ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)carbamate [ No CAS ]
  • [ 267875-62-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydrogen bifluoride / methanol; water / 0 - 20 °C 2: palladium diacetate; potassium carbonate; XPhos / water; toluene / 22 h / 85 °C / Inert atmosphere
  • 3
  • [ 24424-99-5 ]
  • [ 267875-62-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 2.25 h / -78 - 20 °C 1.2: 1 h / 0 °C 1.3: 0 - 20 °C 2.1: potassium hydrogen bifluoride / methanol; water / 0 - 20 °C 3.1: palladium diacetate; potassium carbonate; XPhos / water; toluene / 22 h / 85 °C / Inert atmosphere
  • 4
  • [ 1314538-55-0 ]
  • [ 128810-31-1 ]
  • [ 267875-62-7 ]
  • 5
  • [ 1953-54-4 ]
  • [ 267875-62-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; 1,2-dimethoxyethane / 0.17 h / 0 - 20 °C 1.2: 16 h / 0 - 20 °C 2.1: chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium carbonate / <i>tert</i>-butyl alcohol; water / 3 h / 85 °C / Inert atmosphere
  • 6
  • [ 1314538-55-0 ]
  • [ 1432739-35-9 ]
  • [ 267875-62-7 ]
  • 7
  • [ 24424-99-5 ]
  • [ 81881-74-5 ]
  • [ 267875-62-7 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In water; <i>tert</i>-butyl alcohol at 20℃; for 2.5h; 177 Synthesis of tert-butyl ((1H-indol-5-yl)methyl)carbamate Synthesis of tert-butyl ((1H-indol-5-yl)methyl)carbamate To a solution of (1H-indol-5-yl)methanamine (300 mg, 2.05 mmol) in t-BuOH (20 mL) was added H2O (1 mL), Et3N (214 mg, 2.11 mmol) and (Boc)2O (784 mg, 3.60 mmol). The reaction mixture was stirred at room temperature for 2.5 h. Then the mixture was concentrated in vacuo. Water (40 mL) was added and the mixture was extracted with EtOAc (50 mL*3). The combined organic layers were concentrated to give the crude product, which was purified by silica gel chromatography (PE/EtOAc=5/1) to give tert-butyl ((1H-indol-5-yl)methyl)carbamate as an orange oil (498 mg, yield: 98%). ESI-MS [M+Na]+: 247.1.
88% In acetonitrile at 20℃; for 48h; Inert atmosphere;
  • 8
  • [ 267875-62-7 ]
  • trans-3-(5-aminomethyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 0.67 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / Cooling with ice; Inert atmosphere 2.1: piperidine / methanol / 20 h / Inert atmosphere; Reflux 3.1: trifluoroacetic acid / methanol / 48 h / Inert atmosphere; Reflux
  • 9
  • [ 267875-62-7 ]
  • C22H23N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.67 h / 0 - 20 °C / Inert atmosphere 1.2: 0.5 h / Cooling with ice; Inert atmosphere 2.1: piperidine / methanol / 20 h / Inert atmosphere; Reflux
  • 10
  • [ 267875-62-7 ]
  • [ 33513-42-7 ]
  • C15H18N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: tert-butyl ((1H-indol-5-yl)methyl)carbamate; N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: With water; sodium hydroxide for 0.5h; Cooling with ice; Inert atmosphere;
  • 11
  • [ 15861-24-2 ]
  • [ 24424-99-5 ]
  • [ 267875-62-7 ]
YieldReaction ConditionsOperation in experiment
55% With hydrogen In methanol at 20℃; 113 To a solution of lH-indole-5-carbonitrile (13.9 g, 97.7 mmol, 1.0 eq) in MeOH (280 mL) was added B0C2O (42.6 g, 196 mmol, 2.0 eq) and Raney Ni (about 1.4 g). The mixture was hydrogenated at rt under 50 Psi overnight. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was purified on silica gel column (PE/EA = 10/1 to 4/1) to afford tert-butyl ((lH-indol-5- yl)methyl)carbamate as a yellow oil (13.2 g, 55%).
  • 12
  • [ 267875-62-7 ]
  • tert-butyl ((3-chloro-1H-indol-5-yl)methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With N-chloro-succinimide In dichloromethane at 20℃; for 0.5h; 177 Synthesis of tert-butyl ((3-chloro-1H-indol-5-yl)methyl)carbamate Synthesis of tert-butyl ((3-chloro-1H-indol-5-yl)methyl)carbamate A solution pf tert-butyl ((1H-indol-5-yl)methyl)carbamate (498 mg, 2.02 mmol) and NCS (243 mg, 182 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 0.5 h. The reaction was quenched with water (30 mL) and extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the crude product, which was purified by silica gel chromatography (PE/EtOAc=5/1) to give tert-butyl ((3-chloro-1H-indol-5-yl)methy)carbamate (453 mg, 81%) as a colorless oil. ESI-MS [M+Na]: 281.2.
65% With N-chloro-succinimide; hydrogen In dichloromethane at 0 - 20℃; 113 To a solution of tert-butyl ((lH-indol-5-yl)methyl)carbamate (13.2 g, 53.6 mmol, 1.0 eq) in DCM (140 mL) was added portions NCS (7.13 g, 53.6 mmol, 1.0 eq) at 0 °C. The mixture was hydrogenated at rt overnight. The mixture was concentrated to dryness under reduced pressure. The residue was purified on silica gel column (PE/EA = 10/1 to 4/1) to afford tert-butyl ((3-chloro-lH-indol-5-yl)methyl)carbamate as a white solid (9.7 g, 65%).
  • 13
  • [ 353-83-3 ]
  • [ 267875-62-7 ]
  • C16H19F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With bis(acetylacetonato)palladium(II); norbornene; potassium hydrogencarbonate; 1,3-diphenylpropanedione In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; regioselective reaction;
  • 14
  • [ 267875-62-7 ]
  • (3-chloro-1H-indol-5-yl)methanamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-chloro-succinimide / dichloromethane / 0.5 h / 20 °C 2: hydrogenchloride / water; ethanol; dichloromethane / 5 h / 20 °C
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