Potassium Phosphate, Tribasic → HCID 67317559, compound

HRID 1013319Notes

Reaction equation

HRID 1013319 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=1)[C:6]([C:25]([O:27]CC)=[O:26])=[C:5]2[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]([CH3:38])[CH3:37].[C:39]1(B(O)O)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O[Pd]OC(=O)C)(=O)C>[CH:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:3]=2)[N:7]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:6]=1[C:25]([OH:27])=[O:26])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 67316608HCID 67316608, compound

Product 1

HCID 67317559HCID 67317559, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 5-chloro-3-(2-isopropylphenyl)-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (the synthesis of this compound was similar to the intermediate described in EXAMPLE 134) (56 mg), phenylboronic acid (26 mg), diacetoxypalladium (2.39 mg), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (8.74 mg) and K3PO4 (67.8 mg) was heated at 180° C. in a CEM microwave synthesizer for 1 hour. The reaction was concentrated and the residue was purified by flash chromatography, eluting with 0-50% dichloromethane in hexane. The collected desired ester was saponified with NaOH in tetrahydrofuran-methanol-H2O at 50° C. overnight to provide the title compound. 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ 12.76 (s, 1H), 8.17 (d, J=8.29 Hz, 1H), 7.86 (d, J=7.67 Hz, 1H), 7.78 (d, J=8.90 Hz, 1H), 7.43-7.58 (m, 6H), 7.32-7.44 (m, 5H), 7.28 (t, J=7.21 Hz, 1H), 7.22 (d, J=1.84 Hz, 1H), 7.16-7.21 (m, 1H), 7.06-7.12 (m, 1H), 6.87 (d, J=7.36 Hz, 1H), 4.95 (t, J=7.06 Hz, 2H), 4.21 (t, J=6.14 Hz, 2H), 2.68-2.82 (m, J=7.06 Hz, 1H), 2.37-2.47 (m, 2H), 1.03 (d, J=6.75 Hz, 3H), 0.96 (d, J=6.75 Hz, 3H).

Workup

  1. customthe synthesis of this compound
  2. concentrationThe reaction was concentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with 0-50% dichloromethane in hexane
  5. customThe collected desired ester

Sources & evidence

ORD record
ord-c70431ed52564e5abb542555c1ef6c52
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

Loading…