Cesium carbonate → Methyl 4-(indan-5-ylamino)-5-methylthiothiophene-2-carboxylate

HRID 2298688Notes

Reaction equation

HRID 2298688 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=1[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:64][C:65]1[CH:66]=[C:67]2[C:71](=[CH:72][CH:73]=1)[CH2:70][CH2:69][CH2:68]2>C1(C)C=CC=CC=1>[CH2:70]1[C:71]2[C:67](=[CH:66][C:65]([NH:64][C:2]3[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=3[CH3:7])=[CH:73][CH:72]=2)[CH2:68][CH2:69]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 90496Indan-5-amineHCID 634876Binap, (A+-)-HCID 86583861Methyl 4-bromo-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758690Methyl 4-(indan-5-ylamino)-5-methylthiothiophene-2-carboxylateYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The same procedure as in Example 254, step (a) was followed using 120 mg (0.449 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate (as prepared in Example 241, step (a), 41 mg (10 mol %) of tris-(dibenzylidineacetone)dipalladium, 42 mg (15 mol %) of racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 205 mg (0.629 mmol) of cesium carbonate and 74.8 mg (0.56 mmol) of 5-aminoindan in 900 μL of toluene, and chromatographed as before using 40% CH2Cl2-hexane to afford 100 mg (73%) of the title compound as a yellow resin. 1H-NMR (CDCl3, 400 MHz) δ2.05-2.12 (m, 2H), 2.85-2.90 (m, 4H), 3.86 (s, 3H), 6,09 (s, 1H), 6.82 (d, 1H, J=8.0 Hz), 6.93 (s, 1H), 7.14 (d, 1H, J=8.0 Hz), 7.70 (s, 1H).

Workup

  1. customchromatographed as

Sources & evidence

ORD record
ord-fe66b8657f19412a83c78772d8893b96
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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