Triethylamine → Benzyl (S)-(1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

HRID 2205609Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[N:13]([CH3:14])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C@@H:8]([NH2:10])[CH3:9].C(N(CC)CC)C.[C:22](Cl)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[N:13]([CH3:14])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C@@H:8]([NH:10][C:22](=[O:23])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:9]

Participants

Conditions

Temperature: 13 °C

Procedure

To a stirred solution of (S)-1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethan-1-amine (1.0 g, 3.93 mmol) in DCM (20 mL) was added triethylamine (796 mg, 7.87 mmol) followed by CbzCl (808 mg, 4.72 mmol) at 0° C. The reaction mixture was stirred at about 0 to 26° C. for 1.5 hours. After the solvent was removed, the residue was purified by silica gel column chromatography (PE/EtOAc=10:1) to give the title compound as a yellow oil (1.44 g, 94.7%).

Workup

customAfter the solvent was removed
customthe residue was purified by silica gel column chromatography (PE/EtOAc=10:1)

Sources & evidence

ORD record: ord-dd63baf00f14405a8cabb7d0234a3f50
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371321B2

Reaction notes

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