Dimethylformamide → HCID 117779507, compound

HRID 2206550Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([NH:21][CH2:22][C:23]3[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=3[CH3:29])=[O:20])=[C:11]2[CH3:32])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:33][N:34](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:33]([C:2]1[CH:3]=[C:4]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([NH:21][CH2:22][C:23]3[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=3[CH3:29])=[O:20])=[C:11]2[CH3:32])[CH3:9])[CH:5]=[CH:6][CH:7]=1)#[N:34]

Participants

Conditions

Temperature: 100 °C

Procedure

1-(1-(3-bromophenyl)ethyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1H-indole-3-carboxamide (Compound 171; 100 mg, 0.2 mmol), Zn(CN)2 (36 mg, 0.3 mmol), Pd(PPh3)4 (47 mg, 0.04 mmol) were combined in 2 ml DMF, then stirred at 100° C. for 30 min under N2 in m.w. After the complete of the reaction, purified by pre-HPLC (A: CH3CN, B:water+0.1% HCl. A:B=32:62 ASB C18 150*25 mm) to afford the title compound (35 mg, yield: 40%), 1H NMR (400 MHz, Methanol-d4) δ 7.78 (d, J=8 Hz, 1H), 7.67 (d, J=7.2 Hz, 1H), 7.54 (m, 3H), 7.13 (m, 1H), 7.03 (d, J=4 Hz, 2H), 6.45 (s, 1H), 6.04 (m, 1H), 4.61 (s, 2H), 2.66 (s, 3H), 2.52 (s, 3H), 2.36 (s, 1H), 2.02 (d, J=7.2 Hz, 3H).

Workup

customAfter the complete of the reaction
custompurified by pre-HPLC (A: CH3CN, B

Sources & evidence

ORD record: ord-12084187b54e446287da217fb2928d01
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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