Bis(pinacolato)diborane → HCID 67448984, compound

HRID 1853776Notes

Reaction equation

HRID 1853776 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:32]1[C:33]2[C:34]3[CH:47]=[CH:46][S:45][C:35]=3[C:36](=[O:44])[NH:37][C:38]=2[CH:39]=[CH:40][C:41]=1[O:42][CH3:43]>>[CH3:43][O:42][C:41]1[CH:40]=[CH:39][C:38]2[NH:37][C:36](=[O:44])[C:35]3[S:45][CH:46]=[CH:47][C:34]=3[C:33]=2[C:32]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 27952731-(4-Bromophenyl)CyclopropanecarbonitrileHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67448984HCID 67448984, compoundYield 29%

Procedure

Following General Procedure B, 1-(4-bromophenyl)cyclopropanecarbonitrile (1.5 g, 7.1 mmol) was reacted with bis(pinacolato)diboron (2.7 g, 10 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.3 g, 4.2 mmol) to afford the desired product (378 mg, 29%) as a white solid: ESI MS m/z 373 [C22H16N2O2S+H]+.

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-4500a56248094fcda410b3cda719fcf9
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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