Trifluoroacetic acid → HCID 57794646, compound

HRID 2099835Notes

Reaction equation

HRID 2099835 reaction equation
[CH3:1][O:2][C:3](/[C:5](/NC(=O)OC(C)(C)C)=[CH:6]/[C:7]1[CH:15]=[C:14]([CH3:16])[C:13]2[C:9](=[CH:10][N:11]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:12]=2)[CH:8]=1)=[O:4].FC(F)(F)C(O)=[O:36].C([BH3-])#N.[Na+].O1CCCC1>ClCCl.C(OCC)(=O)C>[CH3:22][Si:21]([CH3:24])([CH3:23])[CH2:20][CH2:19][O:18][CH2:17][N:11]1[CH:10]=[C:9]2[C:13]([C:14]([CH3:16])=[CH:15][C:7]([CH2:6][CH:5]([OH:36])[C:3]([O:2][CH3:1])=[O:4])=[CH:8]2)=[N:12]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 70857175HCID 70857175, compound

Product 1

HCID 57794646HCID 57794646, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (Z)-1-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)vinylcarbamate (200 mg, 0.43 mmol) in dichloromethane (2 mL) at 0° C. was added trifluoroacetic acid (1 mL). The ice bath was removed. After 30 min, the reaction was poured into a separatory funnel containing ethyl acetate and water, neutralized with solid sodium bicarbonate, and the layers were separated. The organic phase was washed with saturated sodium bicarbonate, then brine, dried over magnesium sulfate, and concentrated. The yellow residue was treated with sodium cyanoborohydride (200 mg, 7.4 equiv) and tetrahydrofuran (2 mL). The reaction was stirred at room temperature overnight, diluted with ethyl acetate, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography on silica gel (25% ethyl acetate/hexanes) gave 20.4 mg (13%) as a light yellow oil. Mass spec.: 365.40 (MH)+.

Workup

  1. customThe ice bath was removed
  2. additionthe reaction was poured into a separatory funnel
  3. additioncontaining ethyl acetate and water
  4. customthe layers were separated
  5. washThe organic phase was washed with saturated sodium bicarbonate
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. washwashed with water (2×)
  9. dry with materialbrine, dried over magnesium sulfate
  10. concentrationconcentrated
  11. customColumn chromatography on silica gel (25% ethyl acetate/hexanes) gave 20.4 mg (13%) as a light yellow oil

Sources & evidence

ORD record
ord-ae85c716f83342b6ade06637a8e96e48
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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