Iodobenzene → HCID 57419551, compound

HRID 2353229Notes

Reaction equation

HRID 2353229 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.O(C(C)(C)C)[Na]>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]>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:18]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 43461626HCID 43461626, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 57419551HCID 57419551, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound (120 mg, 34%) was prepared from the compound from step 2 (277 mg, 1 mmol) and iodobenzene (204 mg, 1 mmol) in the presence of Pd2(dba)3 (27 mg, 0.03 mmol), PtBu3 (60 mg. 0.3 mmol) and NaO-t-Bu (96 mg, 1 mmol) by the procedure described in step 3 of Example 1 MS (ESI) m/z 354 (M+H); 1H NMR (400 MHz, CDCl3) δ 1.87 (m, 2H), 2.36-2.43 (m, 4H), 2.61 (b, 4H), 3.14 (b, 4H), 3.68 (s, 3H), 6.80-6.93 (m, 5H), 7.04 (d, J=8.8 Hz, 2H), 7.20 (t, J=8.0 Hz, 2H).

Sources & evidence

ORD record
ord-5ef0a46d1de6467aa3a2b2aa641d2d88
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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