Cesium fluoride → HCID 178520199, compound

HRID 1797153Notes

Reaction equation

HRID 1797153 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:16]=[C:15]([CH:17]3[CH2:19][CH2:18]3)[NH:14][N:13]=2)=[O:10])=[CH:4][CH:3]=1.[F-].[Cs+].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>COCCOC.CO.COCCOC.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>[C:2]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[NH:13][N:14]=[C:15]([CH:17]3[CH2:19][CH2:18]3)[CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 22176755HCID 22176755, compound

Product 1

HCID 178520199HCID 178520199, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×HCID 86595564Dimethoxyethane methanolSolvent

Conditions

Temperature
80 °C

Procedure

To 40 mg of 2-(4-bromophenyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)acetamide resin linked 1 ml of a 10.4M solution of CsF in DME:MeOH (3:1), phenylboronic acid (0, 12 mmol) in DME (0.5 ml) and tetrakis triphenylphosphine palladium, (Pd(PPh3)4, 0.008 mmol) in DME (1 ml) were added. The mixture was shaken 18 hrs at 80° C. and then washed with DMF (3×5 ml), MeOH (3×5 ml) and DCM (3×5 ml). To the resin 5 ml of TFA 10% in DCM were added and the mixture was shaken 1 hr at room temperature, the organic phase was filtered off and the resin was washed with DCM (3×5 ml) and DMSO (2×5 ml). The organic fractions were collected and evaporated under reduced pressure and the residue was analyzed by HPLC-MS (area count 90%, 254 nm; M+1=318, 2M+1=365) without further purification.

Workup

  1. washwashed with DMF (3×5 ml), MeOH (3×5 ml) and DCM (3×5 ml)
  2. additionTo the resin 5 ml of TFA 10% in DCM were added
  3. stirringthe mixture was shaken 1 hr at room temperature
  4. filtrationthe organic phase was filtered off
  5. washthe resin was washed with DCM (3×5 ml) and DMSO (2×5 ml)
  6. customThe organic fractions were collected
  7. customevaporated under reduced pressure
  8. customthe residue was analyzed by HPLC-MS (area count 90%, 254 nm; M+1=318, 2M+1=365) without further purification

Sources & evidence

ORD record
ord-a98d4cc035b44d34a4a3af073c2f2645
Source dataset
uspto-grants-2006_04
Patent number
US07034049B1

Reaction notes

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