Dimethylformamide → HCID 67324111, compound

HRID 1397252Notes

Reaction equation

HRID 1397252 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3([CH2:19][NH2:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:21][N:22](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:20][CH2:19][C:13]1([C:10]2[S:11][CH:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:21]#[N:22])=[CH:3][CH:4]=3)[N:9]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 67323489HCID 67323489, compound

Product 1

HCID 67324111HCID 67324111, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

(4-(4-(4-Bromophenyl)thiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (200 mg, 0.56 mmol), zinc cyanide (53 mg, 0.45 mmol), and DMF (2 mL) were placed in microwave tube and degassed. 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride (41 mg, 0.05 mmol) was added. Reaction was microwaved at 200° C. for 10 min intervals until complete. The reaction was quenched with ammonium hydroxide/water (1:4) and washed with ethyl acetate. Organic layer was dried over sodium sulfate. Crude was purified using silica chromatography with an ethyl acetate wash followed by 10% Methanol in dichloromethane with 1% triethylamine to yield 4-(2-(4-(aminomethyl)tetrahydro-2H-pyran-4-yl)thiazol-4-yl)benzonitrile (20 mg, 10% yield). MS (ESI) m/z: Calculated for C16H17N3OS: 299.11. found: 300.1 (M+H)+.

Workup

  1. customdegassed
  2. customReaction
  3. customwas microwaved at 200° C. for 10 min intervals until complete
  4. customThe reaction was quenched with ammonium hydroxide/water (1:4)
  5. washwashed with ethyl acetate
  6. dry with materialOrganic layer was dried over sodium sulfate
  7. customCrude was purified
  8. washwash

Sources & evidence

ORD record
ord-cb34ccb0818142ba9b4c2f81a717e00b
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…