Formaldehyde → HCID 86725267, compound

HRID 1478869Notes

Reaction equation

HRID 1478869 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][C:11]([NH:13][CH:14]([B:27]3[O:35][CH:34]4[C:29]([CH3:39])([CH:30]5[CH2:36][CH:32]([CH2:33]4)[C:31]5([CH3:38])[CH3:37])[O:28]3)[CH2:15][C:16]3[C:17]([O:25][CH3:26])=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([OH:21])=[O:20])=[O:12])=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[CH2:40]=O>[Pd].CO>[CH3:26][O:25][C:17]1[C:16]([CH2:15][CH:14]([NH:13][C:11](=[O:12])[CH2:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[CH2:1][N:2]([CH3:40])[CH2:3]3)[B:27]2[O:35][CH:34]3[C:29]([CH3:39])([CH:30]4[CH2:36][CH:32]([CH2:33]3)[C:31]4([CH3:38])[CH3:37])[O:28]2)=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 86725265HCID 86725265, compound

Product 1

HCID 86725267HCID 86725267, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-[2-(2-2,3-Dihydro-1H-isoindol-5-yl-acetylamino)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-ethyl]-2-methoxy-benzoic acid (0.110 g, 0.207 mmol), formaldehyde (37% in H2O, 0.06 mL, 0.740 mmol), and methanol (2.5 mL) was purged with argon. Palladium on carbon (10%, 0.049 g) was added, the flask evacuated, and the reaction placed under hydrogen for 18 hr. The reaction mixture was filtered through a Celite-plugged filter frit, washed with CH3OH and CH2Cl2, and concentrated. The crude product was carried forward without purification. ESI-MS m/z 547 (MH)+.

Workup

  1. customthe flask evacuated
  2. filtrationThe reaction mixture was filtered through a Celite-plugged filter frit
  3. washwashed with CH3OH and CH2Cl2
  4. concentrationconcentrated
  5. customThe crude product was carried forward without purification

Sources & evidence

ORD record
ord-9939bb51bf5c4629b908707efd42f048
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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