Acetonitrile → HCID 86643711, compound

HRID 1098654Notes

Reaction equation

HRID 1098654 reaction equation
[NH2:1][CH:2]1[CH2:14][C:13]2[C:12]3[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]=2[CH2:4][CH2:3]1.C(#N)C.[CH3:25][CH2:26][CH2:27]CCCC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][CH:2]1[CH2:14][C:13]2[C:12]3[C:7](=[C:8]([CH2:27][CH:26]=[CH2:25])[CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]=2[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 8900HeptaneHCID 86643712HCID 86643712, compound

Product 1

HCID 86643711HCID 86643711, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred and degassed solution of an appropriately protected ethyl (3-amino-8-bromo-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate derivative of Structure 2c (0.2 mmol) and Pd(PPh3)4 (0.02 mmol, 0.1 eq.) in dry DMF (1.5 ml) is added under inert atmosphere the appropriate tetraC1-5-alkyltin or allyltrialkyltin, respectively (0.22 mmol, 1.1 eq.). The reaction mixture is allowed to stir overnight at 110° C. After cooling to rt, acetonitrile (1 ml) and heptane (1 ml) are added. The acetonitrile-DMF phase is washed three times with heptane. Water is then added and the resulting aq. phase is extracted twice with AcOEt. The combined org. phases are washed with brine and dried over Na2SO4. Evaporation of the solvent in vaccuo yields the protected ethyl (3-amino-8-C1-5-alkyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate derivative or ethyl (3-amino-8-allyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate derivative of Structure 1, respectively.

Workup

  1. stirringto stir overnight at 110° C
  2. washThe acetonitrile-DMF phase is washed three times with heptane
  3. additionWater is then added
  4. extractionthe resulting aq. phase is extracted twice with AcOEt
  5. washphases are washed with brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent in vaccuo

Sources & evidence

ORD record
ord-2712432cb7d04036822c08af7dcdf833
Source dataset
uspto-grants-2012_03
Patent number
US08143304B2

Reaction notes

Loading…