Bis(pinacolato)diborane → HCID 67446789, compound

HRID 1853782Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH3:9])=[CH:4][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]>>[CH:11]1([NH:10][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:35]3[C:36]4[C:37]5[CH:50]=[CH:49][S:48][C:38]=5[C:39](=[O:47])[NH:40][C:41]=4[CH:42]=[CH:43][C:44]=3[O:45][CH3:46])=[CH:3][CH:4]=2)[CH3:9])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Reactant 3

HCID 2733548Bis(pinacolato)diborane

HCID 43177392HCID 43177392, compound

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67446789HCID 67446789, compoundYield 97.3%

Procedure

Following General Procedure E, N-[1-(4-bromophenyl)ethyl]cyclopentanamine (600 mg, 2.3 mmol) was reacted with bis(pinacolato)diboron (410 mg, 1.6 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (250 mg, 0.81 mmol) to afford the desired product (330 mg, 97%) as a brown solid: 1H NMR (300 MHz, CD3OD) δ 7.73-7.64 (m, 2H), 7.60-7.50 (m, 2H), 7.47-7.34 (m, 3H), 6.01 (d, J=5.4 Hz, 1H), 4.57 (q, J=6.8 Hz, 1H), 3.74 (s, 3H), 3.62-3.45 (m, 1H), 2.30-2.02 (m, 2H), 1.93-1.85 (m, 2H), 1.81 (d, J=6.7 Hz, 3H), 1.77-1.51 (m, 4H).

Workup

customto afford the crude boronic ester which

Sources & evidence

ORD record: ord-4760a946a1504a758161f62e4656a37a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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