HCID 67393677, compound → HCID 71295656, compound

HRID 1776802Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:25][CH2:24][CH2:23][N:15]4[C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[CH:22]=[C:14]4[C:13]=3[CH:26]=2)O1.Br[C:29]1[C:30]([N:49]([CH3:54])[S:50]([CH3:53])(=[O:52])=[O:51])=[CH:31][C:32]2[O:36][C:35]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[C:34]([C:44]([NH:46][CH3:47])=[O:45])[C:33]=2[CH:48]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:26]1[C:13]2[C:14]3[N:15]([CH2:23][CH2:24][O:25][C:12]=2[CH:11]=[CH:10][C:9]=1[C:29]1[C:30]([N:49]([CH3:54])[S:50]([CH3:53])(=[O:52])=[O:51])=[CH:31][C:32]2[O:36][C:35]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)=[C:34]([C:44]([NH:46][CH3:47])=[O:45])[C:33]=2[CH:48]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[CH:22]=3

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of compound 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydrobenzo[6,7][1,4]oxazepino[4,5-a]indole (72 mg, 0.2 mmol), 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (91 mg, 0.2 mmol), K3PO4-3H2O (160 mg, 0.6 mmol) and Pd(dppf)Cl2 (15 mg, 0.02 mmol) in 2 mL of DMF was stirred at 90° C. for 8 h under N2, then the mixture was purified using prep-HPLC to provide Compound 42 (30 mg, yield: 24.9%). 1H-NMR (CDCl3, 400 MHz) δ 7.92˜7.97 (m, 3H), 7.81 (s, 1H), 7.63˜7.65 (m, 2H), 7.33 (d, J=8.0 Hz, 2H), 7.12˜7.25 (m, 5H), 6.97 (s, 1H), 6.00 (d, J=4.0 Hz, 1H), 4.62 (t, J=4.2 Hz, 2H), 4.54 (t, J=4.2 Hz, 2H), 3.18 (s, 3H), 3.00 (d, J=4.8 Hz, 3H), 2.72 (s, 3H). MS (M+H)+: 610.

Workup

customthe mixture was purified

Sources & evidence

ORD record: ord-d7d3a37b05d141ee83ce65b373a28c2d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

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