Water → HCID 66712666, compound

HRID 1262437Notes

Reaction equation

HRID 1262437 reaction equation
Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([S:11][CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[C:13]([O:17][CH2:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Na+].[Na+].O.CN(C)C=O>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:13]([O:17][CH2:18][C:19]1[CH:24]=[C:23]([C:2]2[N:10]3[C:5]([CH:6]=[N:7][C:8]([S:11][CH3:12])=[N:9]3)=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 37738083-tert-Butoxymethylphenylboronic acidHCID 574161287-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66712666HCID 66712666, compound

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.370 g, 1.52 mmol), 3-(tert-Butoxymethyl)phenylboronic acid (0.564 g, 2.71 mmol), Bis(tri-tert-butylphosphine)palladium (47 mg, 0.092 mmol), 2.00 M of Sodium Carbonate in Water (3.0 mL, 6.0 mmol), and N,N-Dimethylformamide (12.0 mL, 155 mmol) were combined in a reaction vial, partially degassed and backfilled with Nitrogen, and the mixture was heated at 60° C. overnight under an atmosphere of Nitrogen. The reaction mixture was diluted with water (25 mL) and DCM (25 mL). The aqueous was extracted with DCM (2×, 10 mL) and combined organics diluted with 1:1 EtOAc:hexane (50 mL), followed by washes with water (2×, 25 mL) and brine (25 mL). The organics were dried over sodium sulfate and conc. in vacuo to afford 7-(3-tert-Butoxymethyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine which was then oxidized, analogous to Example 1504a, to afford 7-(3-tert-Butoxymethyl-phenyl)-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine (398 mg, 73%). 1H-NMR (DMSO-d6): 9.37 (s, 1H), 8.22 (s, 1H), 8.10 (d, 1H, J=7.77 Hz), 7.81 (d, 1H, J=4.97 Hz), 7.53 (t, 1H, J=7.77 Hz), 7.44 (d, 1H, J=4.97 Hz), 7.41 (d, 1H, J=7.77 Hz), 4.50 (s, 2H), 3.46 (s, 3H), 1.26 (s, 9H).

Workup

  1. custompartially degassed
  2. additionThe reaction mixture was diluted with water (25 mL) and DCM (25 mL)
  3. extractionThe aqueous was extracted with DCM (2×, 10 mL)
  4. additioncombined organics diluted with 1:1 EtOAc
  5. dry with materialThe organics were dried over sodium sulfate and conc. in vacuo

Sources & evidence

ORD record
ord-49f1211ef8394d01bb408d704b2e3897
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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