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

HRID 84447Notes

Reaction equation

HRID 84447 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[CH:23]=[CH:22][CH:21]=[C:20](B3OC(C)(C)C(C)(C)O3)[C:19]=2[CH:18]=[N: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:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[CH:18]=[N:17][NH:16]2

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 579002002-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine

Product 1

HCID 442423644-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-1h-indazole

Procedure

2-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine from Example 73 was reacted with indazole 4-boronic acid pinacol ester using standard Suzuki coupling procedure. Purification on prep HPLC and triturating with hexanes gave 140. 1H NMR (400 MHz, CDCl3): 3.34 (2H, t), 4.42 (2H, t), 7.07-7.11 (2H, m), 7.18-7.22 (1H, m), 7.35 (1H, s), 7.42-7.49 (3H, m), 7.79 (1H, dd), 8.50 (1H, s). MS: (ESI+) 319

Workup

  1. customPurification on prep HPLC
  2. customtriturating with hexanes

Sources & evidence

ORD record
ord-a8f3cebf4ac54806aa3f792cd7965e34
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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