Potassium Carbonate → HCID 89717937, compound

HRID 1480753Notes

Reaction equation

HRID 1480753 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10](Cl)[C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=3)[NH:13][C:12]=2[N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB(/[CH:34]=[CH:35]/[CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)O1.C(=O)([O-])[O-].[K+].[K+]>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>[CH2:1]([C:8]1[N:9]=[C:10](/[CH:34]=[CH:35]/[CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=3)[NH:13][C:12]=2[N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 89717673HCID 89717673, compoundHCID 89717993HCID 89717993, compound

Product 1

HCID 89717937HCID 89717937, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

In a 2-5 mL microwave vial was added methyl 2-benzyl-4-chloro-9H-pyrimido[4,5-b]indole-7-carboxylate (0.100 g, 0.284 mmol), (E)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)piperidine (0.113 g, 0.426 mmol), potassium carbonate (0.106 g, 0.768 mmol) and Pd(Ph3P)4 (0.05 g, 0.044 mmol). The vial was purged with N2 (3 vacuum+refill cycles). DME (2.84 mL) and water (0.398 mL) were added and the vial was flushed with N2 (one vacuum+refill) and then heated to 110° C. while stirred for 24 hours. After cooling, the mixture was concentrated to dryness under reduced pressure and the residue was purified by flash chromatography to give (E)-methyl 2-benzyl-4-(4-(piperidin-1-yl)but-1-en-1-yl)-9H-pyrimido[4,5-b]indole-7-carboxylate (55 mg, 0.121 mmol, 42.6% yield) as a light yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 2H) 1.50-1.61 (m, 4H) 2.30-2.47 (m, 4H) 2.53-2.59 (m, 2H) 2.59-2.70 (m, 2H) 3.91 (s, 3H) 4.27 (s, 2H) 7.16-7.24 (m, 1H) 7.29 (t, J=7.6 Hz, 2H) 7.34-7.43 (m, 4H) 7.88 (dd, J=8.2, 1.4 Hz, 1H) 8.07 (d, J=1.4 Hz, 1H) 8.41 (d, J=8.2 Hz, 1H) 12.48 (s, 1H); HRMS m/z 455.2442 (M+H)+; HPLC 100% @ 220 nm and 99.4% @ 254 nm, RT=1.84 minutes.

Workup

  1. customThe vial was purged with N2 (3 vacuum+refill cycles)
  2. additionDME (2.84 mL) and water (0.398 mL) were added
  3. customthe vial was flushed with N2 (one vacuum+refill)
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated to dryness under reduced pressure
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b1b772d297c24dac9fc3b825c482dc97
Source dataset
uspto-grants-2016_08
Patent number
US09409906B2

Reaction notes

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