1,2-Dichloroethane → HCID 11624283, compound

HRID 550408Notes

Reaction equation

HRID 550408 reaction equation
C(Cl)CCl.[NH:5]([C:7]1[C:8]2[N:9]([CH:17]=[CH:18][CH:19]=2)[C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:6].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29](O)=[O:30].C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.O>[CH:17]1[N:9]2[C:10]3[C:15]([N:16]=[C:7]([NH:5][NH:6][C:29]([C:21]4[NH:20][C:28]5[C:23]([CH:22]=4)=[CH:24][CH:25]=[CH:26][CH:27]=5)=[O:30])[C:8]2=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 72899Indole-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 10679460HCID 10679460, compound

Product 1

HCID 11624283HCID 11624283, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of EDC (94 mg, 0.49 mmol) and DMAP (cat.) in ethyl acetate (15 mL), compound 14a (77 mg, 0.39 mmol) and 2-indolecarboxylic acid (63 mg, 0.39 mmol) were added, portion wise, within 15 minutes. The resulting mixture was stirred at room temperature for 24 h, then shaken with sodium bicarbonate saturated solution and water. Evaporation of the dried extract gave a residue which was crystallized to give compound 6 as a white solid (82 mg, 62% yield); mp 186° C. (dichloromethane/light petroleum); IR (KBr) 3255, 1680 cm−1; 1H NMR (DMSO-d6) 6.75 (s, 1H), 7.05 (m, 1H), 7.20 (m, 4H), 7.40 (m, 3H), 7.65 (m, 1H), 8.10 (m, 1H), 8.35 (s, 1H), 9.55 (bs, 1H), 10.65 (bs, 1H), 11.80 (bs, 1 H). MS (CI) m/z 342 (MH+). Anal. Calcd. for C20H15N5O: C, H, N.

Workup

  1. customEvaporation of the dried
  2. extractionextract
  3. customgave a residue which
  4. customwas crystallized

Sources & evidence

ORD record
ord-e056f74f23df4c2ba3ab8744b73e76f5
Source dataset
uspto-grants-2011_05
Patent number
US07947682B2

Reaction notes

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