Potassium Carbonate → HCID 59750689, compound

HRID 747965Notes

Reaction equation

HRID 747965 reaction equation
[C:1]([NH:8][CH2:9][CH:10]1[C:18]2[C:13](=[CH:14][C:15](O)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=1.[C:29]([O-:32])([O-])=O.[K+].[K+].[NH4+].[Cl-].[CH3:37]C(N(C)C)=O>>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH:10]1[C:18]2[C:13](=[C:14]([O:32][C:29]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:37]1)([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 5

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 66673443HCID 66673443, compound2×

Product 1

HCID 59750689HCID 59750689, compound

Procedure

Combine N-Boc-1-aminomethyl-indan-5-ol (described in prep for Intermediate 17) (5.80 g, 20.9 mmol), 6-chloronicotinonitrile (2.89 g, 20.9 mmol), K2CO3 (4.33 g, 31.3 mmol) and DMA (50 ml) and heat at 100 C for 4.5 hours. After cooling, pour the reaction mixture into saturated, aqueous NH4Cl and extract with EtOAc (2×). Wash extract with brine, dry (MgSO4) and concentrate to a brown foam. Purify on silica gel (30% EtOAc/Hexane) to obtain the title compound (7.88 g) as a light yellow foam. Mass spectrum (ion spray): m/z=380 (M+1); 1HNMR (CDCl3): 8.45 (s, 1H), 7.90 (d, 1H), 7.25-7.18 (m, 2H), 6.99 (d, 1H), 6.91 (d, 1H), 4.69 (m, 1H), 3.51-3.25 (m, 2H), 3.03 (m, 1H), 2.62-2.39 (m, 1H), 1.83-1.68 (m, 4H), 1.46 (s, 9H).

Workup

  1. temperatureAfter cooling
  2. extractionextract with EtOAc (2×)
  3. washWash
  4. extractionextract with brine
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate to a brown foam
  7. customPurify on silica gel (30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-895eacf1cdc3468898905968f541f08c
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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