Potassium Bromide → HCID 71277736, compound

HRID 62117Notes

Reaction equation

HRID 62117 reaction equation
[C:1]([C:3]1[S:4][C:5]2[C:11]([C:12]#[N:13])=[C:10](/[N:14]=[CH:15]/[N:16](C)C)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[O:19]1[C:23]2[CH:24]=[CH:25][C:26](N)=[CH:27][C:22]=2[CH2:21][CH2:20]1.[K+].[Br-]>CCOC(C)=O>[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([NH:13][C:12]3[C:11]4[C:10](=[CH:9][CH:8]=[C:6]5[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]5=4)[N:14]=[CH:15][N:16]=3)=[CH:27][C:22]=2[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 38411022,3-Dihydro-1-benzofuran-5-amineHCID 178484237HCID 178484237, compound

Product 1

HCID 71277736HCID 71277736, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared from VII and 2,3-dihydro-1-benzofuran-5-amine. Flash chromatography eluent (EtOAc). Yield: 95%; yellow solid; mp 216° C.; IR (KBr) νmax/cm−1 2894, 2853, 2228, 1643, 1609, 1579, 1484, 1467, 1376, 1353, 1306, 1269, 1219, 1192, 1164, 1123, 978, 941, 881, 814; 1H NMR (300 MHz, DMSO-d6) δ 8.49 (d, 1H, J=8.7 Hz), 8.10 (s, 1H), 7.75 (d, 1H, J=8.7 Hz), 7.22 (m, 1H), 7.04 (s, 1H), 6.78 (m, 1H), 4.53 (t, 2H, J=8.7 Hz), 3.20 (t, 1H, J=8.7 Hz); HRMS calcd for C18H12N5OS (M+H+): 346.0763, found 346.0762.

Sources & evidence

ORD record
ord-886cd0ab74064f7c9da2860b934dd2e3
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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