Triethylamine → Cyclopropanecarboxylic acid [6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide

HRID 545547Notes

Reaction equation

HRID 545547 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH2:24])[CH2:7][C:6]2=1.[CH2:25](N(CC)CC)[CH3:26].Cl.O.CCO[C:37]([CH3:39])=[O:38]>ClCCl>[Br:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH:24][C:37]([CH:39]3[CH2:26][CH2:25]3)=[O:38])[CH2:7][C:6]2=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 574316706-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-ylamine hydrochlorideHCID 86605536EtOAc water HCl

Product 1

HCID 59161198Cyclopropanecarboxylic acid [6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amideYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix 6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-ylamine hydrochloride (195 mg, 0.48 mmol), triethylamine (210 μL, 1.5 mmol), cyclopropanecarbonyl chloride chloride (55 μL, 0.6 mmol) in dichloromethane (10 mL) and stir at room temperature for 18 h. Shake the reaction with dilute HCl/water/EtOAc. Dry (MgSO4) the organic layer and concentrate to give 120 mg crude product. Recrystallize (EtOH) to give 50 mg (24%) of the title compound. MS (ES): m/z 441, 443 (M+1); 1H NMR (CDCl3): δ 7.63 (s, 1H), 7.27 (m 2H), 7.08 (d,1H), 6.92 (t, 1H), 6.75 (d, 1H), 6.63 (d, 1H), 5.58 (br d, 1H), 5.23 (s, 2H), 4.44 (br m, 1H), 3.13 (dd, 1H), 2.74 (m, 2H), 2.64 (dd,1H), 2.23 (m,2H), 2.16 (m,1H), 2.02 (m,1H), 1.09 (m,4H); HPLC: Rt=3.55 min, (95%).

Workup

  1. dry with materialDry (MgSO4) the organic layer
  2. concentrationconcentrate
  3. customto give 120 mg crude product
  4. customRecrystallize (EtOH)

Sources & evidence

ORD record
ord-b686813e2b56419d842d5753eca62a5b
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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