Sodium Hydroxide → HCID 86673446, compound

HRID 2362424Notes

Reaction equation

HRID 2362424 reaction equation
[C:1](=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH2:2].[OH-].[Na+].Cl[O:12]C(C)(C)C.CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.[Br:75][C:76]1[CH:81]=[CH:80][CH:79]=[C:78](/[CH:82]=[CH:83]/[C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][C:85]=2[F:90])[N:77]=1>C(O)CC.O>[Br:75][C:76]1[N:77]=[C:78]([C@@H:82]([NH:2][C:1](=[O:8])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[C@@H:83]([C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][C:85]=2[F:90])[OH:12])[CH:79]=[CH:80][CH:81]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 77922tert-Butyl carbamateHCID 521297Tert-Butyl hypochloriteHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 86673445HCID 86673445, compound

Product 1

HCID 86673446HCID 86673446, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent3×

Conditions

Temperature
0 °C

Procedure

To tert-butyl carbamate (270 mg, 2.31 mmol) in propanol (3 mL) was added sodium hydroxide (91 mg, 2.27 mmol) in water (6 mL) followed by tert-butyl hypochlorite (0.256 mL, 2.27 mmol). The solution was cooled to 0° C. and (DHQD)2PHAL (34.8 mg, 0.045 mmol) was added in propanol (3 mL) followed by (E)-2-bromo-6-(2-fluorostyryl)pyridine (207 mg, 0.744 mmol) in propanol (6 mL). To this was added potassium osmate dihydrate (10.97 mg, 0.030 mmol) as a solid in one portion. The reaction was allowed to gradually warm to room temperature in the dewar overnight. The reaction was cooled to 0° C. and quenched by addition of sodiumthiosulfate (300 mg) in water (3 mL). The reaction was stirred at room temperature for 30 min. The reaction was diluted with ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (15%→30% EtOAc/Hex) gave 375 mg (quant.). Mass spec.: 411.2 (MH)+.

Workup

  1. temperatureto gradually warm to room temperature in the dewar overnight
  2. temperatureThe reaction was cooled to 0° C.
  3. customquenched by addition of sodiumthiosulfate (300 mg) in water (3 mL)
  4. additionThe reaction was diluted with ether
  5. washwashed with water (2×)
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. customColumn chromatography (15%→30% EtOAc/Hex) gave 375 mg (quant.)

Sources & evidence

ORD record
ord-814325361903490c8158fbc8b0919fcc
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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