Trifluoroacetic acid → HCID 59394250, compound

HRID 450250Notes

Reaction equation

HRID 450250 reaction equation
C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.[CH2:15]([O:22][CH2:23][C:24]1[N:29]=[CH:28][N:27]=[C:26]([O:30][C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[NH:36][CH:35]=[CH:34]3)[CH:25]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([O:22][CH2:23][C:24]1[N:29]=[CH:28][N:27]=[C:26]([O:30][C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[NH:36][CH2:35][CH2:34]3)[CH:25]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 593942601H-Indole, 5-[[6-[(phenylmethoxy)methyl]-4-pyrimidinyl]oxy]-

Product 1

HCID 59394250HCID 59394250, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylsilane (4 mL, 24.7 mmol) and TFA (6 mL) are added to 5-(6-benzyloxymethyl-pyrimidin-4-yloxy)-1H-indole (0.22 g, 0.682 mmol) in 6 mL of acetonitrile and stirred at rt overnight. The reaction is concentrated to an oil that is dissolved in EtOAc and washed with a saturated aqueous sodium bicarbonate. The organic layer is removed, dried, and concentrated to an to obtain crude 5-(6-benzyloxymethyl-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole. MS (ESI) m/z 334.2 (M+1).

Workup

  1. concentrationThe reaction is concentrated to an oil that
  2. dissolutionis dissolved in EtOAc
  3. washwashed with a saturated aqueous sodium bicarbonate
  4. customThe organic layer is removed
  5. customdried
  6. concentrationconcentrated to

Sources & evidence

ORD record
ord-4c51f94576cd4327a8ecfbc06c84e6c8
Source dataset
uspto-grants-2013_07
Patent number
US08486954B2

Reaction notes

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