Triethylamine → HCID 66760619, compound

HRID 564218Notes

Reaction equation

HRID 564218 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([Sn](CCCC)(CCCC)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1)CCC.C(N(CC)CC)C>CN(C=O)C.ClCCl>[N:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[C:2]1[S:6][C:5]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 6077842-(Tributylstannyl)pyridineHCID 66759641HCID 66759641, compound

Product 1

HCID 66760619HCID 66760619, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of EXAMPLE 10A (184 mg), tri-ortho-tolylphosphine (52 mg), tris(dibenzylidineacetone)dipalladium(0) (52 mg), 2-(tri-n-butylstannyl)pyridine (420 mg) and triethylamine (238 L) in DMF (5 mL) was heated at 75° C. overnight. The mixture was cooled, diluted with dichloromethane and flash chromatographed (with 0-15% methanol in 2:1 ethyl acetate/hexane). Additional purification by HPLC (Zorbax, C-18, Mobile phase A: 0.1% TFA in H2O; B: 0.1% TFA in acetonitrile; 0-100% gradient) provided the title compound. 1H NMR (DMSO-d6) δ 7.34-7.39 (m, 2H), 7.74-7.76 (m, 2H), 7.86-7.95 (m, 3H), 8.00-8.05 (m, 1H), 8.02 (s, 1H), 8.60 (d, J=4.6 Hz, 1H), 9.04 (brs, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. customchromatographed (with 0-15% methanol in 2:1 ethyl acetate/hexane)
  3. customAdditional purification by HPLC (Zorbax, C-18, Mobile phase A: 0.1% TFA in H2O; B: 0.1% TFA in acetonitrile; 0-100% gradient)

Sources & evidence

ORD record
ord-2fdcee5f191a465e87136abf4c70a768
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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