Isocyanate → HCID 86673804, compound

HRID 1527181Notes

Reaction equation

HRID 1527181 reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8](C(N=[N+]=[N-])=O)=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[N-:19]=[C:20]=[O:21]>C1(C)C=CC=CC=1>[F:18][CH:2]([F:1])[O:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([N:19]=[C:20]=[O:21])=[CH:9][NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 105034IsocyanateHCID 86673805HCID 86673805, compound

Product 1

HCID 86673804HCID 86673804, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 1-carbamoyl-6-difluoromethoxy-1H-indole-3-carboxylic acid (180 mg, 0.66 mmol) in THF (6 mL) was added Et3N (111 μl, 0.8 mmol) and the resulting solution was stirred at RT under nitrogen for 10 min. DDPA (220 μl, 0.8 mmol) was added and the reaction was further stirred at RT under nitrogen for 3 h. TLC indicated consumption of the starting material. The reaction mixture was concentrated and the crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1 to 1:1) to give 6-difluoromethoxy-1H-indole-3-carbonyl azide (MS: 251 [M−H]−; tR (HPLC conditions k): 3.57 min) and 1-carbamoyl-6-difluoromethoxy-1H-indole-3-carbonyl azide (MS: 251 [M−CONH2]−; 268 [M−N2]+; tR (HPLC conditions k): 3.46 min). 6-Difluoromethoxy-1H-indole-3-carbonyl azide intermediate was suspended in toluene (6 mL) and refluxed under nitrogen for 3 h until completion of the reaction. The crude isocyanate was used as was in the next step.

Workup

  1. temperaturerefluxed under nitrogen for 3 h until completion of the reaction

Sources & evidence

ORD record
ord-b75b8ea56514464dba08d7244dff612d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…