Cesium carbonate → HCID 68287864, compound

HRID 593284Notes

Reaction equation

HRID 593284 reaction equation
F[C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[C:33]([O:40][CH3:41])[CH:32]=1>CN(C=O)C.CCOC(C)=O.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]>[C:20]([NH:19][S:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:2]2[CH:7]=[C:6]([C:34]3[CH:35]=[CH:36][C:31]([F:30])=[CH:32][C:33]=3[O:40][CH3:41])[CH:5]=[CH:4][N:3]=2)[CH:11]=1)(=[O:18])=[O:17])([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 31628383-Amino-N-tert-butylbenzene-1-sulfonamideHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 68287864HCID 68287864, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-fluoro-4-iodopyridine (100 mg, 0.45 mmol), 3-amino-N-(tert-butyl)benzenesulfonamide (153 mg, 0.67 mmol), and Cs2CO3 (291 mg, 0.89 mmol) in dry DMF (3 mL) was heated at 150° C. for 1.5 h in a microwave oven. After addition of (4-fluoro-2-methoxyphenyl)boronic acid (152 mg, 0.89 mmol) the mixture was degassed with a stream of nitrogen for 5 minutes. Pd(dppf)Cl2 (73 mg, 0.09 mmol) was added and the reaction mixture was heated to 140° C. for 90 minutes in a microwave oven. The mixture was diluted with EtOAc and washed twice with sat. aq. NaHCO3-solution and once with brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure, and the residue was purified by preparative HPLC (water/ACN 95:5 to 0:100) to yield the desired product D2 as a yellow solid (9 mg, 5%). 1H NMR (400 MHz, d6-DMSO, 300K) δ 1.12 (s, 9H), 3.82 (s, 3H), 6.89 (m, 2H), 6.97 (s, 1H), 7.06 (dd, J=11.5 Hz, J=2.4 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H), 7.39 (m, 2H), 7.44 (s, 1H), 7.87 (d, J=8.0 Hz, 1H), 8.18 (d, J=5.4 Hz, 1H), 8.24 (m, 1H), 9.39 (s, 1H). MS (ES) C22H24FN3O3S requires: 429. found: 430 (M+H)+.

Workup

  1. customwas degassed with a stream of nitrogen for 5 minutes
  2. temperaturethe reaction mixture was heated to 140° C. for 90 minutes in a microwave oven
  3. washwashed twice with sat. aq. NaHCO3-solution and once with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by preparative HPLC (water/ACN 95:5 to 0:100)

Sources & evidence

ORD record
ord-c55b9e75be5e4f4da25ab333fd8ca1a5
Source dataset
uspto-grants-2016_01
Patent number
US09242937B2

Reaction notes

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