2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide → HCID 71509400, compound

HRID 1776823Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:17][C:16](=[O:18])[N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[CH:15]=[C:7]3[C:6]=2[CH:19]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:28][C:29]3[CH:39]=[C:38]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42])[C:37](B4OC(C)(C)C(C)(C)O4)=[CH:36][C:30]=3[C:31]=2[C:32]([NH:34][CH3:35])=[O:33])=[CH:23][CH:22]=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]>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:28][C:29]3[CH:39]=[C:38]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:42])=[O:43])[C:37]([C:2]4[CH:3]=[CH:4][C:5]5[O:17][C:16](=[O:18])[N:8]6[C:9]7[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=7[CH:15]=[C:7]6[C:6]=5[CH:19]=4)=[CH:36][C:30]=3[C:31]=2[C:32]([NH:34][CH3:35])=[O:33])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-6H-benzo[5,6][1,3]oxazino[3,4-a]indol-6-one (47 mg, 0.15 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (51 mg, 0.1 mmol), K3PO43H2O (80 mg, 0.3 mmol) and Pd(dppf)Cl2 (7 mg, 0.01 mmol) in 2 mL of DMF was heated in a microwave reactor at 100° C. for 20 minutes, and then the mixture was purified using prep-HPLC to provide Compound 53 (2.7 mg, yield: 4.4%). 1H-NMR (CDCl3, 400 MHz) δ 8.52 (d, J=7.6 Hz, 1H), 8.07 (s, 1H), 7.92˜7.96 (m, 3H), 7.70 (d, J=7.6 Hz, 1H), 7.62 (s, 1H), 7.41˜7.54 (m, 4H), 7.21˜7.23 (m, 2H), 7.12 (s, 1H), 5.89 (s, 1H), 3.11 (s, 3H), 3.00 (d, J=4.8 Hz, 3H), 2.88 (s, 3H). MS (M+H)+: 610.

Workup

customthe mixture was purified

Sources & evidence

ORD record: ord-8017bc5dc10f42998fac0ce9150df4a9
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

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