1-(Azidomethyl)-3-(trifluoromethyl)benzene → HCID 66958255, compound

HRID 1424678Notes

Reaction equation

HRID 1424678 reaction equation
[F:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][I:12])[N:5]=[C:4]([C:13]2[N:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)[N:3]=1.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[CH2:24][N:25]=[N+:26]=[N-:27]>>[F:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[N:27]=[N:26][N:25]([CH2:24][C:23]3[CH:28]=[CH:29][CH:30]=[C:21]([C:20]([F:19])([F:32])[F:31])[CH:22]=3)[C:11]=2[I:12])[N:5]=[C:4]([C:13]2[N:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

3

Reactant 2

HCID 212826681-(Azidomethyl)-3-(trifluoromethyl)benzeneHCID 66957826HCID 66957826, compound

Product 1

HCID 66958255HCID 66958255, compound

Procedure

Synthesized from 2-fluoro-4-(3-iodoprop-2-ynyloxy)-6-(1-methyl-1H-pyrrol-2-yl)-1,3,5-triazine and 3-trifluoromethyl-benzylazide using general procedure; 0.311 g, 0.556 mmol, 80%; mp=185-187° C. (dec.); IR (υ[cm−1]) 3130, 3059, 1595, 1555, 1418, 1357, 1173, 1104, 1056, 911, 803, 756; 1H NMR (600 MHz, CDCl3) δ=7.61-7.58 (m, 2H), 7.50-7.41 (m, 3H), 6.90 (s, 1H), 6.21 (dd, J=3.9, 2.5, 1H), 5.64 (s, 2H), 5.56 (s, 2H), 4.09 (s, 3H); 13C NMR (151 MHz, CDCl3) δ=171.5 (dd, J=361.1, 15.4), 171.3, 169.8, 135.0, 133.0, 131.6 (q, J=32.8), 131.5, 129.9, 125.9 (q, J=3.6), 125.1 (q, J=3.7), 123.9 (q, J=272.4), 121.5, 81.6, 61.7, 54.0, 39.0; HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C18H15F4IN7O, 560.0313; found 560.0311.

Sources & evidence

ORD record
ord-a4bb4010f9834157b9cb2d8a66c4c0ee
Source dataset
uspto-grants-2015_01
Patent number
US08927736B2

Reaction notes

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