Triphenyl phosphite → HCID 67448110, compound

HRID 1960138Notes

Reaction equation

HRID 1960138 reaction equation
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]([NH2:9])=[C:6]([NH2:8])[CH:7]=1.[C:11]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34](O)=O)[CH:30]=[CH:31][CH:32]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>N1C=CC=CC=1>[C:11]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:14]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]3[NH:8][C:34]([CH2:33][C:29]4[CH:30]=[CH:31][CH:32]=[C:27]([Br:26])[CH:28]=4)=[N:9][C:5]=3[CH:4]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 7540Triphenyl phosphiteHCID 74653(3-Bromophenyl)acetic acidHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 574814674-Chloro-5-iodobenzene-1,2-diamine2×

Product 1

HCID 67448110HCID 67448110, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a microwave vial containing a solution of Intermediate 11-1 (which was prepared from 5-chloro-4-iodo-1,2-phenylenediamine (Intermediate 1-6 of Example 1) and 4-biphenylboronic acid following the procedures of Step 9 in Example 1) (500 mg, 1.7 mmol) in pyridine 8 mL was added 3-bromo-phenyl acetic acid (365 mg, 1.7 mmol), followed by triphenyl phosphite (0.58 mL, 2.2 mmol). The reaction was run in a microwave reactor at 220° C. for 10 min. The solvent was partially removed in vacuo, then diluted with EtOAc (75 mL) and washed three times with 50 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo, and then purified by chromatography over silica (eluting with EtOAc/Hexanes=1/1) to give the title compound 14-1 as a tan solid.

Workup

  1. customThe solvent was partially removed in vacuo
  2. additiondiluted with EtOAc (75 mL)
  3. washwashed three times with 50 mL portions of saturated aqueous ammonium chloride
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography over silica (eluting with EtOAc/Hexanes=1/1)

Sources & evidence

ORD record
ord-839953d6c0214a98ae0d30b7060073c7
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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