Formamide → HCID 86641783, compound

HRID 555704Notes

Reaction equation

HRID 555704 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([S:17]([OH:19])=[O:18])=[CH:13][CH:12]=1.C[Si](Cl)(C)C.[CH:26]([NH2:28])=[O:27]>C1(C)C=CC=CC=1.CC#N>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:5]([S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:20])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[NH:28][CH:26]=[O:27])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 713FormamideHCID 6397ChlorotrimethylsilaneHCID 10818p-Toluenesulfinic acidHCID 7363353-Chloro-2-fluorobenzaldehyde

Product 1

HCID 86641783HCID 86641783, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Intermediate 16.2 is prepared in analogy to a published literature procedure (Chem. Lett. 1988, 9, 1531-1534). A mixture of 3-chloro-2-fluorobenzaldehyde (2.00 g, 12.6 mmol), p-toluenesulfinic acid (2.96 g, 18.9 mmol), TMSCl (1.75 mL, 13.9 mmol) and formamide (1.25 mL, 31.5 mmol) in toluene (7 mL) and CH3CN (7 mL) is heated at 50° C. for 5h. After completion, the reaction mixture is quenched by H2O, EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless powder; HPLC: AtRet=4.21 min; 1HNMR(CDCl3) 8.18 (s, 1H), 7.72 (d, 2H), 7.50-7.45 (m, 1H), 7.40-7.30 (m, 3H), 7.20-7.10 (m, 1H), 7.00 (d, 1H), 6.60 (d, 1H), 2.45 (s, 3H).

Workup

  1. customAfter completion, the reaction mixture is quenched by H2O, EtOAc
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1884386368f94dce94e874a6a11ba180
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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