Triethylamine → 4-(3-Chloro-indazole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide

HRID 1178939Notes

Reaction equation

HRID 1178939 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[F:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16][NH:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:26]([C:23]2[CH:22]=[CH:21][C:20]([C:18]([NH:17][CH2:16][C:15]3[CH:30]=[CH:31][C:12]([F:11])=[CH:13][CH:14]=3)=[O:19])=[CH:25][CH:24]=2)(=[O:27])=[O:28])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 958943-Chloro-1H-indazoleHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 589751524-(3-Chloro-indazole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 3-chloro-1H-indazole (120 mg, 0.79 mmol) and 4-(4-fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (114 mg, 0.35 mmol) in CH2Cl2 (2.0 mL) and treat with Et3N (50 L, 0.36 mmol). Stir the solution for 1 h at RT, then dilute with additional CH2Cl2 (20.0 mL) and wash with satd aq. NaHCO3 (15 mL). Dry, filter, and concentrate the organic phase and purify the crude material by flash chromatography (100% hexanes to 50% EtOAc/hexanes linear gradient) to give the title compound (129 mg, 83%) as a white foam. MS (ES+) 443.9 (M+1)+, (ES−) 442.0 (M−1)−. 1H NMR (400 MHz, CDCl3): δ 8.17 (d, 1H, J=8.3), 8.03 (d, 2H, J=8.2), 7.83 (d, 2H, J=8.9), 7.64 (m, 2H), 7.41 (t, 1H, J=7.4), 7.27 (m, 2H), 7.01 (t, 2H, J=8.9), 6.31 (br s, 1H), 4.57 (d, 2H, J=5.9).

Workup

  1. washwash with satd aq. NaHCO3 (15 mL)
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate the organic phase
  5. custompurify the crude material by flash chromatography (100% hexanes to 50% EtOAc/hexanes linear gradient)

Sources & evidence

ORD record
ord-33349d63e2504f7980b104abe6d22953
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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