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

HRID 84456

Reaction equation

HRID 84456 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.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[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:18]1[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 579002002-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine

Product 1

HCID 442424903-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)pyridine

Procedure

2-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine from Example 73 was reacted with 3-pyridine boronic acid pinacol ester using standard Suzuki coupling procedure. Purification on silica gave 152. 1H NMR (400 MHz, CDCl3): 3.29 (2H, t), 4.39 (2H, t), 7.05-7.10 (2H, m), 7.18-7.22 (2H, m), 7.32-7.35 (1H, m), 7.74 (1H, dd), 7.89 (1H, dt), 8.55 (1H, dd), 8.91 (1H, s). MS: (ESI+) 280

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-dcdbe97a5dda422dbd216bfe2506c2bc
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Linked notes

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