3,3-Dimethyl-1-butyne → 8-Bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1949929Notes

Reaction equation

HRID 1949929 reaction equation
[N:1]([C:4]1[S:5][C:6]2[CH2:7][CH2:8][O:9][C:10]3[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:11]=3[C:12]=2[N:13]=1)=[N+:2]=[N-:3].[CH3:19][C:20]([CH3:24])([CH3:23])[C:21]#[CH:22]>>[Br:18][C:16]1[CH:15]=[CH:14][C:11]2[C:12]3[N:13]=[C:4]([N:1]4[C:21]([C:20]([CH3:24])([CH3:23])[CH3:19])=[CH:22][N:3]=[N:2]4)[S:5][C:6]=3[CH2:7][CH2:8][O:9][C:10]=2[CH:17]=1

Participants

3

Reactant 2

HCID 135123,3-Dimethyl-1-butyneHCID 579001042-Azido-8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Product 1

HCID 579003598-Bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Procedure

Following the procedure for 414, Step 3, 2-azido-8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene was reacted with 3,3-dimethyl-1-butyne to afford the title compound as a pale yellow solid. LCMS (Method A): RT=4.95 min, [M+H]+=405 and 407. 1H NMR (CDCl3): 8.16 (1 H, dd, J=8.1, 0.9 Hz), 7.55 (1 H, s), 7.28 (2 H, m), 4.42 (2 H, t, J=5.1 Hz), 3.37 (2 H, t, J=5.1 Hz), 1.54 (9 H, s).

Sources & evidence

ORD record
ord-ec464b17d8cc44bb8e4147a775db8aaf
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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