Dimethylformamide → HCID 59199232, compound

HRID 2079689Notes

Reaction equation

HRID 2079689 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[CH:20][CH:19]=1)[N:13]=[CH:12]2)(=O)=O.C(N(CC)CC)C.C([SiH](CC)CC)C.CN([CH:47]=[O:48])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]>[CH:47]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH2:25])(=[O:27])=[O:26])=[CH:22][CH:23]=1)[N:13]=[CH:12]2)=[O:48]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 12052TriethylsilaneHCID 59199239HCID 59199239, compound

Product 1

HCID 59199232HCID 59199232, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
85 °C

Procedure

A mixture of 2-(4-sulfamoylphenylamino)quinazolin-8-yl trifluoromethanesulfonate (900 mg, 2 mmole), Pd(dppf)Cl2 (170 mg, 0.2 mmole), triethylamine (700 ul, 5 mmole) and triethylsilane (960 ul, 6 mmole) in DMF (20 ml) was placed in a stainless steel reactor. CO was bubbled into the mixture in the reactor. The reaction solution was stirred at 85° C. under CO (420 psi) for overnight. The reaction mixture was poured into 80 ml of saturated NaHCO3 and extracted with ethyl acetate (2×250 ml). The combined organic layers were washed with water (2×60 ml) and brine (60 ml), then dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography to give 4-(8-formylquinazolin-2-ylamino)benzenesulfonamide (274 mg, 0.83 mmole) as brown solid. ES/MS m/z 328.9 (MH+).

Workup

  1. customwas placed in a stainless steel reactor
  2. customCO was bubbled into the mixture in the reactor
  3. additionThe reaction mixture was poured into 80 ml of saturated NaHCO3
  4. extractionextracted with ethyl acetate (2×250 ml)
  5. washThe combined organic layers were washed with water (2×60 ml) and brine (60 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-095ffb9fb18a46138248570a7aee7880
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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