Chloroform → HCID 178518305, compound

HRID 2236822Notes

Reaction equation

HRID 2236822 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:16]=[C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24](I)[CH:25]=3)[C:20](=[O:28])[NH:19][C:18]2=[O:29])=[CH:11][CH:10]=1.[S:30]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31]1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)(Cl)Cl.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:16]=[C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:32]4[CH:33]=[CH:34][S:30][CH:31]=4)[CH:25]=3)[C:20](=[O:28])[NH:19][C:18]2=[O:29])=[CH:11][CH:10]=1

Participants

9

Reactant 6

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 581760Thiophene-3-boronic acidHCID 178518341HCID 178518341, compound

Product 1

HCID 178518305HCID 178518305, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-{[4-(2-Hydroxymethyl-pyrrolidin-1-ylmethyl)-phenylamino]-methylene}-6-iodo-4H-isoquinoline-1,3-dione (200 mg, 0.40 mmol) in N,N-dimethylformamide (10 mL) were added 3-thienylboronic acid (120 mg, 0.94 mmol) and Na2CO3 (216 mg, 2.0 mmol). Pd2(dba)3.CHCl3 (20 mg, 0.02 mmol) and P(tBu)3.HBF4 (19 mg, 0.06 mmol) were then added. The mixture is then degassed and heated at 100° C. for 1 h. The N,N-dimethylformamide is then evaporated under reduced pressure and the residue is taken up in EtOAc and H2O. The EtOAc layer is dried and evaporated. The residue, which resulted, is subjected to chromatography to provide the desired product (90 mg, 49%). MS (ESI): 460.2 (M+1)+1

Workup

  1. customThe mixture is then degassed
  2. customThe N,N-dimethylformamide is then evaporated under reduced pressure
  3. dry with materialThe EtOAc layer is dried
  4. customevaporated
  5. customThe residue, which resulted

Sources & evidence

ORD record
ord-317ee83535df457cb37f546236ac679c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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