1-(Azidomethyl)-3-(trifluoromethyl)benzene → HCID 44517948, compound

HRID 1424683Notes

Reaction equation

HRID 1424683 reaction equation
[Br:1][C:2]1[C:6]([Br:7])=[N:5][N:4]([CH:8]2[N:12]([CH2:13][C:14]#[C:15][I:16])[C:11](=[O:17])[CH2:10][CH2:9]2)[N:3]=1.[F:18][C:19]([F:31])([F:30])[C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[CH2:23][N:24]=[N+:25]=[N-:26]>>[Br:7][C:6]1[C:2]([Br:1])=[N:3][N:4]([CH:8]2[N:12]([CH2:13][C:14]3[N:26]=[N:25][N:24]([CH2:23][C:22]4[CH:27]=[CH:28][CH:29]=[C:20]([C:19]([F:18])([F:31])[F:30])[CH:21]=4)[C:15]=3[I:16])[C:11](=[O:17])[CH2:10][CH2:9]2)[N:5]=1

Participants

3

Reactant 2

HCID 212826681-(Azidomethyl)-3-(trifluoromethyl)benzeneHCID 44517947HCID 44517947, compound

Product 1

HCID 44517948HCID 44517948, compound

Procedure

Synthesized from 5-(4,5-dibromo-2H-1,2,3-triazol-2-yl)-1-(3-iodoprop-2-ynyl)pyrrolidin-2-one and 3-trifluoromethyl-benzylazide using general procedure; 0.663 g, 0.982 mmol, 93%; mp=105-110° C. (dec.); IR (υ[cm−1]) 3002, 2104, 1696, 1415, 1327, 1166, 1123, 1074, 921, 829, 753, 702; 1H NMR (600 MHz, CDCl3) δ=7.59 (d, J=7.8, 1H), 7.56 (s, 1H), 7.48 (t, J=7.7, 1H), 7.40 (d, J=7.7, 1H), 6.16 (d, J=7.6, 1H), 5.59 (d, J=3.3, 2H), 4.88 (d, J=15.7, 1H), 3.92 (d, J=15.7, 1H), 2.95-2.86 (m, 1H), 2.65-2.56 (m, 1H), 2.49 (dd, J=17.1, 9.9, 1H), 2.43-2.36 (m, 1H); 13C NMR (151 MHz, CDCl3) δ=175.0, 147.0, 135.1, 131.6 (m), 131.5, 129.9, 126.1, 125.8 (m), 125.1 (m), 123.9 (m), 79.6, 78.3, 53.9, 36.4, 28.6, 25.6; HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C17H14Br2F3IN7O, 673.8618; found 673.8613.

Sources & evidence

ORD record
ord-25ddaaa3939b4347bb7a2c81c4eb9e67
Source dataset
uspto-grants-2015_01
Patent number
US08927736B2

Reaction notes

Loading…