Sodium Bicarbonate → HCID 57527158, compound

HRID 1671809Notes

Reaction equation

HRID 1671809 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[S:13][CH2:12][CH2:11][CH2:10][S:9]1.[Li]CCCC.Cl.Cl.Cl[CH2:22][C:23]1[N:28]=[C:27]2[S:29][C:30]([NH:32][CH:33]([CH3:35])[CH3:34])=[N:31][C:26]2=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH2:22][C:23]2[N:28]=[C:27]3[S:29][C:30]([NH:32][CH:33]([CH3:35])[CH3:34])=[N:31][C:26]3=[CH:25][CH:24]=2)[S:9][CH2:10][CH2:11][CH2:12][S:13]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 10104703HCID 10104703, compoundHCID 86614199HCID 86614199, compoundHCID 178418339Butyllithium

Product 1

HCID 57527158HCID 57527158, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-fluorophenyl)-1,3-dithiane (2.72 g, 12.7 mmol, 4.4 eq.) in THF (65 mL) under nitrogen at 0° C. was added n-BuLi (1.6M/hexane; 7.4 mL, 11.8 mmol, 4.1 eq.) over 0.5 hr. After another 0.5 hr, the 0° C. bath was removed and replaced by a −78° C. bath. 5-(Chloromethyl)-N-isopropylthiazolo[5,4-b]pyridin-2-amine dihydrochloride (0.90 g, 2.86 mmol, 1.0 eq.) was added in portions after 15 min., and the reaction was stirred for 1.5 hr. Ice, EtOAc and saturated aqueous NaHCO3 were added, and the −78° C. bath was removed. After stirring to room temperature, the layers were separated, and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography using CH2Cl2 followed by CH2Cl2:MeOH (40:1) as eluent afforded 5-((2-(2-fluorophenyl)-1,3-dithian-2-yl)methyl)-N-isopropylthiazolo[5,4-b]pyridin-2-amine as a yellow solid (0.95 g, 79% yield).

Workup

  1. customthe 0° C. bath was removed
  2. customreplaced by a −78° C.
  3. customthe −78° C. bath was removed
  4. stirringAfter stirring to room temperature
  5. customthe layers were separated
  6. dry with materialthe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f669dc2f163e4ff38b3b66c6f974b795
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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