5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → 5-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-1h-pyrrolo[2,3-b]pyridine

HRID 627871Notes

Reaction equation

HRID 627871 reaction equation
Br[C:2]1[S:15][C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[NH:16]1[C:24]2[C:19](=[CH:20][C:21](B3OC(C)(C)C(C)(C)O3)=[CH:22][N:23]=2)[CH:18]=[CH:17]1>>[S:15]1[C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=[C:2]1[C:21]1[CH:20]=[C:19]2[CH:18]=[CH:17][NH:16][C:24]2=[N:23][CH:22]=1

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 579002002-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine

Product 1

HCID 442423615-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-1h-pyrrolo[2,3-b]pyridine

Procedure

2-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine from Example 73 was reacted with 7-azaindole-5-boronic acid pinacol ester using standard Suzuki coupling procedure. Purification on prep HPLC gave 136. 1H NMR (400 MHz, CDCl3): 3.30 (2H, t), 4.40 (2H, t), 6.56-6.58 (1H, m), 7.05-7.07 (2H, m), 7.15-7.18 (2H, m), 7.36 (1H, t), 7.75 (1H, d), 8.16 (1H, d), 8.63 (1H, d). MS: (ESI+) 318

Workup

  1. customPurification on prep HPLC

Sources & evidence

ORD record
ord-66ed16d0a40748488d54afa3ea84fc37
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

Loading…