4-Fluoroaniline → HCID 71277777, compound

HRID 62127Notes

Reaction equation

HRID 62127 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].[F:19][C:20]1[CH:26]=[CH:25][C:23](N)=[CH:22][CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH:13][C:12]2[C:11]3[C:10](=[CH:9][CH:8]=[C:6]4[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]4=3)[N:14]=[CH:15][N:16]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 71277777HCID 71277777, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-fluoroaniline. Flash chromatography eluent (DCM-EtOAc, 5:5). Yield: 92%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3049, 2840, 2226, 1722, 1643, 1610, 1581, 1557, 1502, 1377, 1355, 1305, 1269, 1227, 1208, 1166, 1130, 1090, 981, 846, 829, 818; 19F NMR (282 MHz, DMSO-d6) δ −120.31; 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, 1H, J=9.0 Hz), 8.16 (s, 1H), 7.76 (d, 1H, J=9.0 Hz), 7.26-7.08 (m, 4H); HRMS calcd for C16H9N5SF (M+H+): 322.0563, found 322.0551.

Sources & evidence

ORD record
ord-89afff46f3114f5d8f388c0f3609ee5c
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

Loading…