Water → 7-(aminomethyl)-4-bromo-9H-carbazole-1-carboxamide

HRID 661933Notes

Reaction equation

HRID 661933 reaction equation
[N:1]([CH2:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:10]([Br:21])=[CH:11][CH:12]=[C:13]([C:18]([NH2:20])=[O:19])[C:14]=3[NH:15]2)=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:10]([Br:21])=[CH:11][CH:12]=[C:13]([C:18]([NH2:20])=[O:19])[C:14]=3[NH:15]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86642951HCID 86642951, compound

Product 1

HCID 666063397-(aminomethyl)-4-bromo-9H-carbazole-1-carboxamideYield 123.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Step 2 A mixture of 7-(azidomethyl)-4-bromo-9H-carbazole-1-carboxamide (350 mg, 0.814 mmol), triphenylphosphine (427 mg, 1.627 mmol), and water (18 μL, 0.976 mmol) in THF (10 mL) was heated at 70° C. for 3.5 h. The mixture was cooled to rt and partitioned between EtOAc and 1 M hydrochloric acid. The pH of the aqueous phase was raised to 8-9 with sodium hydroxide pellets, and then was extracted with EtOAc. The organic phase was dried and concentrated to provide crude 7-(aminomethyl)-4-bromo-9H-carbazole-1-carboxamide as a yellow glassy foam (320 mg, 99%). 1H NMR (400 MHz, DMSO-d6) δ 11.61 (1H, br.), 8.47-8.55 (1H, m), 8.19 (1H, br. s.), 7.81-7.84 (1H, m), 7.76 (1H, s), 7.63-7.66 (1H, m), 7.53-7.59 (2H, m), 7.41 (1H, d, J=8.1 Hz), 7.27 (1H, dd, J=8.4, 1.3 Hz), 3.90 (2H, s).

Workup

  1. temperatureThe mixture was cooled to rt
  2. custompartitioned between EtOAc and 1 M hydrochloric acid
  3. temperatureThe pH of the aqueous phase was raised to 8-9 with sodium hydroxide pellets
  4. extractionwas extracted with EtOAc
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26b66e5fc83444f7b2f9cd45e7d4edd5
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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