Proton sponge → HCID 66851098, compound

HRID 1515470Notes

Reaction equation

HRID 1515470 reaction equation
C[Sn](C)(C)[C:3]1[CH:11]=[C:10]2[C:6]([C:7]3[CH2:15][CH2:14][NH:13][C:12](=[O:16])[C:8]=3[NH:9]2)=[CH:5][CH:4]=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][C:37]=1[S:45](=[O:48])(=[O:47])[NH2:46]>O1CCCC1.C(Cl)Cl.[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]>[Cl:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([C:3]2[CH:11]=[C:10]3[C:6]([C:7]4[CH2:15][CH2:14][NH:13][C:12](=[O:16])[C:8]=4[NH:9]3)=[CH:5][CH:4]=2)=[O:41])=[CH:38][C:37]=1[S:45]([NH2:46])(=[O:48])=[O:47]

Participants

7

Reactant 3

HCID 88675Proton spongeHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 58107481HCID 58107481, compound

Product 1

HCID 66851098HCID 66851098, compoundYield 1.8%

Reagents, catalysts & solvents 3

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-CatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Trimethylstannanyl-2,3,4,9-tetrahydro-pyrido[3,4-b]indol-1-one (0.66 g, 1.88 mmol) and 1,8-bis(dimethylamino) naphthalene (0.210 g, 0.94 mmol) in tetrahydrofuran (25 mL) is treated with 4-chloro-3-sulfamoyl-benzoyl chloride (0.48 g, 1.88 mmol). After a few minutes, allylpalladium chloride dimer (0.057 g, 0.15 mmol) is added. The reaction mixture is stirred for 5 min at room temperature and then refluxed for 2 h. After cooling to room temperature the reaction mixture is diluted with methylene chloride and washed with a saturated sodium chloride solution then concentrated in vacuo. Purification by silica gel chromatography (75% ethyl acetate-hexane) followed by recrystallization (ethanol-ethyl acetate) provides 0.014 g (1.8%) of the title compound as a pale yellow solid. 1H NMR (DMSO): δ 12.00 (s, 1H), 8.30 (s, 1H), 8.00 (m, 1H), 7.90 (m, 6H), 7.60 (m, 1H), 3.40 (m, 2H), 3.00 (m, 2H). MS (m/z): 402.0 (M−1).

Workup

  1. waitAfter a few minutes
  2. temperaturerefluxed for 2 h
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. washwashed with a saturated sodium chloride solution
  5. concentrationthen concentrated in vacuo
  6. customPurification by silica gel chromatography (75% ethyl acetate-hexane)
  7. customfollowed by recrystallization (ethanol-ethyl acetate)

Sources & evidence

ORD record
ord-c1eb996862d44b938a255cc1fa3a8dcf
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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