Trifluoroacetic acid → HCID 59375074, compound

HRID 661991Notes

Reaction equation

HRID 661991 reaction equation
[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15](O)([CH3:17])[CH3:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66605841HCID 66605841, compound2×

Product 1

HCID 59375074HCID 59375074, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4-bromo-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (Intermediate 73-2, 300 mg, 0.864 mmol) in DCM (2 mL) was treated with triethylsilane (1.380 mL, 8.64 mmol) and then slowly with TFA (0.666 mL, 8.64 mmol) and the mixture was stirred at rt for 40 min. The resulting suspension was diluted with DCM and the resulting solution was washed with NaHCO3 (aq). The organic phase was washed with water and brine, and dried and concentrated to give 4-bromo-7-isopropyl-9H-carbazole-1-carboxamide as a white solid (280 mg, 98%). 1H NMR (400 MHz, chloroform-d) δ 10.50 (1H, br. s.), 8.63 (1H, d, J=8.1 Hz), 7.32-7.40 (3H, m), 7.22 (1H, dd, J=8.4, 1.3 Hz), 5.97 (2H, br. s.), 3.02-3.18 (1H, m), 1.35 (6H, d, J=6.8 Hz). Mass spectrum m/z 331, 333 (M+H)+.

Workup

  1. washthe resulting solution was washed with NaHCO3 (aq)
  2. washThe organic phase was washed with water and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ac34cb6a152140a68622fc65daf29a6d
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

Loading…