HCID 53443277, compound → HCID 67486266, compound

HRID 1755178Notes

Reaction equation

HRID 1755178 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)C(=O)OC(C)(C)[O:13][C:12]2=O)=[CH:6][CH:5]=1.[O:30]1[C:35]2=[CH:36][CH:37]=[CH:38][C:34]2=[CH:33][CH:32]=[C:31]1[NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN1C(=O)CCC1.O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]([C:12](=[O:13])[N:39]([C:31]2[O:30][C:35]3=[CH:36][CH:37]=[CH:38][C:34]3=[CH:33][CH:32]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 53443277HCID 53443277, compoundHCID 67486710HCID 67486710, compound

Product 1

HCID 67486266HCID 67486266, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-[5-(4-Bromobenzyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl]-benzoic acid methyl ester (1.35 g, 2.93 mmol) and 4-benzofuran-2-ylphenylamine (736 mg, 3.52 mmol) in dry NMP (10 mL) was heated at 220° C. for 5 min in the microwave. The reaction mixture was diluted with water then extracted with EtOAc. After concentrating, the crude material was purified by flash chromatography on silica gel (ISCO cartridge, 40 g), eluting with a gradient of zero to 35% ethyl acetate in hexane over 30 minutes to afford 4-[2-(4-Benzofuran-2-ylphenylcarbamoyl)-3-(4-bromophenyl)-propyl]-benzoic acid methyl ester (935 mg, 56%). 1H NMR (300 MHz, DMSO-d6): δ 9.92 (s, 1H), 7.86 (d, J=8.4 Hz, 2H), 7.80 (d, J=8.7 Hz, 2H), 7.64-7.17 (m, 13H), 3.81 (s, 3H), 3.10-2.93 (m, 3H), 2.85-2.71 (m, 2H).

Workup

  1. extractionthen extracted with EtOAc
  2. concentrationAfter concentrating
  3. customthe crude material was purified by flash chromatography on silica gel (ISCO cartridge, 40 g)
  4. washeluting with a gradient of zero to 35% ethyl acetate in hexane over 30 minutes

Sources & evidence

ORD record
ord-2fe57fddd207495d9467230def235731
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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