Water → 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-N-tert-butylbenzenesulfonamide

HRID 1037689Notes

Reaction equation

HRID 1037689 reaction equation
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])(O)O.C(=O)([O-])[O-].[K+].[K+].O.[NH2:25][C:26]1[N:35]=[C:34]([C:36]([N:38]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39]2)=[O:37])[C:33]2[C:28](=[CH:29][CH:30]=[C:31](I)[CH:32]=2)[N:27]=1>C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:25][C:26]1[N:35]=[C:34]([C:36]([N:38]2[CH2:39][C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:46]2)=[O:37])[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])[CH:32]=2)[N:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 58457195(2-Amino-6-iodoquinazolin-4-yl)isoindolin-2-ylmethanone

Product 1

HCID 467017542-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-N-tert-butylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

1.6 g of 2-borono-N-tert-butylbenzenesulfonamide, 2.66 g of potassium carbonate, 86 μl of water and 196 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride are added to a solution of 2 g of 2-amino-6-iodo-4-(1,3-dihydroisoindol-2-ylcarbonyl)quinazoline in 100 ml of ethanol under argon. The mixture is heated at 120° C. for 16 h, giving a clear solution. The hot solution is filtered through kieselguhr and rinsed with ethanol. The filtrate is evaporated to dryness in vacuo. Crystallisation of the residue from 5 ml of acetonitrile/water gives the product.

Workup

  1. customgiving a clear solution
  2. filtrationThe hot solution is filtered through kieselguhr
  3. washrinsed with ethanol
  4. customThe filtrate is evaporated to dryness in vacuo
  5. customCrystallisation of the residue from 5 ml of acetonitrile/water
  6. customgives the product

Sources & evidence

ORD record
ord-d1667a50c2b64b6fbc17ec0123adfd3f
Source dataset
uspto-grants-2013_10
Patent number
US08546565B2

Reaction notes

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