Cesium carbonate → (+/-)-2-(hydroxy(5-methoxy-7-methyl-1H-indol-4-yl)methyl)benzo[d]thiazole-6-carbonitrile

HRID 2174089Notes

Reaction equation

HRID 2174089 reaction equation
[C:1]([C:3]1[CH:32]=[CH:31][C:6]2[N:7]=[C:8]([CH:10]([OH:30])[C:11]3[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[C:16]4[C:12]=3[CH:13]=[CH:14][N:15]4C(OC(C)(C)C)=O)[S:9][C:5]=2[CH:4]=1)#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].[BH4-].[Na+]>C1COCC1.CO>[OH:30][CH:10]([C:11]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2)[C:8]1[S:9][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:32]=[CH:31][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 4311764Sodium borohydrideHCID 86701724tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

HCID 86701725(+/-)-2-(hydroxy(5-methoxy-7-methyl-1H-indol-4-yl)methyl)benzo[d]thiazole-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (40 mg, 0.089 mmol) and Cs2CO3 (145 mg, 0.445 mmol) were mixed in THF (0.5 mL) and MeOH (0.5 mL), and stirred at 65° C. for 2 hours. NaBH4 (67 mg, 1.78 mmol) was added to the reaction mixture and stirred at rt for 1 hour to reduce the oxidative by-products. The reaction mixture was then concentrated dissolved in MeOH and purified with HPLC (HC-B) to provide the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 8.45 (d, J=1.01 Hz, 1H) 7.92 (d, J=8.59 Hz, 1H) 7.73 (dd, J=8.59, 1.52 Hz, 1H) 7.15 (d, J=3.28 Hz, 1H) 6.62-6.88 (m, 2H) 6.42 (d, J=3.03 Hz, 1H) 3.82 (s, 3H) 2.50 (s, 3H). HRMS calcd. for C13H15N3O2S (M+H)+ 350.0958. found 350.096.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutiondissolved in MeOH
  3. custompurified with HPLC (HC-B)

Sources & evidence

ORD record
ord-3bb97d62ac0c4ddab281b39e311766f4
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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