Bis(pinacolato)diborane → HCID 67447616, compound

HRID 1853798Notes

Reaction equation

HRID 1853798 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9])=[C:4]([F:15])[CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:35]1[C:36]2[C:37]3[CH:50]=[CH:49][S:48][C:38]=3[C:39](=[O:47])[NH:40][C:41]=2[CH:42]=[CH:43][C:44]=1[O:45][CH3:46]>>[F:15][C:4]1[CH:3]=[C:2]([C:35]2[C:36]3[C:37]4[CH:50]=[CH:49][S:48][C:38]=4[C:39](=[O:47])[NH:40][C:41]=3[CH:42]=[CH:43][C:44]=2[O:45][CH3:46])[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9]

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 58901741HCID 58901741, compoundHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67447616HCID 67447616, compoundYield 15.2%

Procedure

Following General Procedure E, 4-bromo-2-fluoro-N-(2-hydroxyethyl)benzenesulfonamide (3.30 mg, 1.1 mmol) was reacted with bis(pinacolato)diborane (300 mg, 1.2 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (310 mg, 1.0 mmol) to afford the desired product (68 mg, 13%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.95 (s, 1H), 8.04 (t, J=5.8 Hz, 1H), 7.93 (t, J=7.8 Hz, 1H), 7.93 (d, J=5.4 Hz, 1H), 7.57 (d, J=9.1 Hz, 1H), 7.49-7.43 (m, 2H), 7.30 (dd, J=8.0, 1.5 Hz, 1H), 5.89 (d, J=5.4 Hz, 1H), 4.78 (t, J=5.6 Hz, 1H), 3.72 (s, 3H), 3.46 (q, J=6.2 Hz, 2H), 3.05 (m, 2H).

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-fef87435760b4b1a956cf84282d41569
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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