N-methyl-2-pyrrolidone → HCID 69309492, compound

HRID 1947026Notes

Reaction equation

HRID 1947026 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:17]3[C:12](=[C:13]([O:18][Si](C(C)C)(C(C)C)C(C)C)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.[F:29][C:30]([F:35])([F:34])[CH2:31]OC.CN1[C:41](=[O:42])[CH2:40]CC1>>[F:35][C:30]([F:29])([F:34])[CH2:31][CH:41]([OH:42])[CH2:40][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]=[CH:10][N:9]2[C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 1363042,2,2-Trifluoroethyl methyl etherHCID 69311915HCID 69311915, compound

Product 1

HCID 69309492HCID 69309492, compound

Procedure

1-(2-methylsulfanyl-pyrimidin-4-yl)-4-triisopropylsilanyloxy-1H-indole (1.25 g) was mixed with 1,1,1-trifluoro-2-methoxy-ethane (2.5 g) and H2CO3 (2.68 g) in NMP (5 mL) at 110° C. for 30 min, cooled to RT, quenched with water, extracted into DCM, and the filtrate purified on a column with hexane to EtOAc/hexane. The fractions collected yielded an oil which was triturated with water to precipitate a solid, which was filtered and dried to yield 4,4,4-tri-fluoro-1-[1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-butan-2-ol (1.5 g).

Workup

  1. customquenched with water
  2. extractionextracted into DCM
  3. customthe filtrate purified on a column with hexane to EtOAc/hexane
  4. customThe fractions collected
  5. customyielded an oil which
  6. customwas triturated with water
  7. customto precipitate a solid, which
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-7b661ca2ea2742c2a9ddfd1efd4da301
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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